P-nitrophenyl dichloroisobutyl ether



Patented Aug. 12, 1947 UNITED STATES PATENT OFFICE P-NITROPHENYLDICHLOROISOBUTYL ETHER William F. Hester, Drexel Hill, and W. E. Craig,Philadelphia, Pa., assignors to Rohm & Haas Company, Philadelphia, Pa.,a corporation of Delaware No Drawing. Application October 25, 1946,Serial N0. 705,800

1 Claim. (Cl. 260-612) l 2 This invention relates to nitrophenyldichlorocelery. It effectively controlled anthracnose on isobutyl etherand has for its object the probeans and Cercospora and Septoria oncelery vision of a compound having both insecticidal Aspray containing1% of p-nitrophenyl dichloand fungicidal actions upon which arepredicated roisobutyl ether was applied to bean plants for utility inpesticidal compositions for use in ho-rti- 5 the control of Mexican beanbeetle larvae. A kill culture and agriculture. of 93% was obtained intwenty-four hours. We have found the compound, Sprays at 0.125% werealso applied to give kills 4-NOzCeI-I4OCI-IzCCHCI-Ia)CHzCl in vamustests averaging A 4% dust gave complete control of Colorado to be arather unique one in such respects. It potato b u larvae. may e p p yreacting P- t Ophenol in the A spray containing 0.25% of p-nitrophenyl ff t Sodium Salt h methallyl chloride to dichloroisobutyl ether wasapplied to potato f py t yl ether d C plants for early blight. While, incontrol plots ating this ether. treated by the common Bordeau sprays,44% y y Of le, chlorine gas was pas 5 of the plants showed evidence ofdisease, only nt 1159 grams f p-nitrop y methallyl ether of the plantsin three test plots treated with th stirring a 5111550161111 Cooling tomaintain the 0.25% spray showed evidence of disease. he temperature ofthe reaction mixture between Compositions for control of both insectsand 29 C. and 37 C. until a Weight increase of 437 fungi on plants maybe prepared as has been ingrams wa Obtained- A Small amount of hydro- 20dicated and applied in the form either of sprays gen chlo ide wasevolved. A reddish-brown oil or of dusts. In addition to the acetonesolution was obtained. This was dissolved in ethy ene used for sprays,there may be made solutions in chloride, and this solution was washedtwice with such solvents as Pine 11 together with an a aq us p as mcarbonate solution and emulsifying or wetting agent, such as a petroleumt en with wat t wa dried Over anhydrous sulfonate, a polyglycerol-fattyacid condensate, potassium carbonate and the solvent removed by or along chained alkylphenoxypolyethoxyheating on a steam bath under reducedpressure. ethanol Busts may be prepared as concentm- There was Obtained1497 grams f a dark-brown tions of 0.25% to 5% in such finely dividedsolids Oil which Wa p p y the desired as talc, clay, chalk, magnesiumcarbonate, walnut phe y dichloruisobutyl ether- The Product as 30 shellflour, and the like. Both sprays and dusts Obtained contained 5.0% ofnitrogen and 29.1% are effective against many commonfungi and inofchlorine. Theoretica1 values are 5.3% and sects on plants 26.8%,respectively. We claim:

This product was dissolved in acetone to form AS a new chemicm compound,

a 25% solution. This solution was stirred into water to yield asuspension which was adjusted 4'NOZCGH4OCH2CCMCH3)CHZCI to one part ofthe ether in 833 parts of water. WILLIAM F. HESTER.

suspension was sprayed onto bean plants and CRAB},

